198 Jessie Caverhill Pass, Oakville

Price: $1,799,900

5 bedrooms, 5 bathrooms

3,000 - 3,499 sqft

Property Type: Detached

MLS#: W12985726

If you've been waiting on the sidelines for the perfect combination of massive living space, untouchable privacy, and incredible value, your wait is officially over. Welcome to 198 Jessie Caverhill Passage-an executive residence on a premium 45-foot lot that checks every single box. This is a rare opportunity, and it is priced to move. Boasting 3,357 square feet of bright, above-ground elegance, this home is built for living large. Step inside to find soaring 9-foot smooth ceilings that carry through both the main and second floors. Stunning, premium hardwood flows flawlessly throughout the entire home. The heart of this property is a true chef's kitchen, fully loaded with upgraded cabinetry, quartz countertops, stainless steel appliances, and a massive center island. That kitchen flows right out into the ultimate game-changer: the backyard. Step outside onto a massive custom deck engineered to host 40 of your closest friends. The best part? You are completely surrounded by towering, mature cedars that deliver total privacy. In this highly sought-after Glenorchy neighborhood, that kind of seclusion is a massive rarity. It's your own private oasis. Head upstairs to find four generously sized bedrooms, including a guest suite featuring a private bath and a charming Juliet balcony. The primary retreat is an absolute showstopper, offering two walk-in closets and a spa-inspired five-piece ensuite complete with a freestanding soaker tub and glass shower. Need more space? Head downstairs to the fully finished, 1,400 square-foot lower level. This complete living suite features a massive rec room, a generous bedroom, a modern full bath, and a functional kitchenette. Whether it's an in-law suite or your premier game day headquarters, the value here is off the charts. With over 4,700 total square feet of finished living space, luxury finishes, and an extremely rare cedar-lined backyard, properties with this kind of immediate upside do not last. Don't sleep on it!

198 Jessie Caverhill Pass - Detached photo 1 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 2 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 3 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 4 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 5 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 6 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 7 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 8 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 9 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 10 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 11 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 12 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 13 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 14 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 15 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 16 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 17 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 18 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 19 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 20 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 21 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 22 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 23 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 24 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 25 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 26 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 27 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 28 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 29 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 30 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 31 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 32 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 33 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 34 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 35 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 36 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 37 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 38 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 39 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 40 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 41 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 42 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 43 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 44 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 45 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 46 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 47 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 48 of 49 in Oakville, Ontario
198 Jessie Caverhill Pass - Detached photo 49 of 49 in Oakville, Ontario
active
New Listing
1/49

$1,799,900 - 198 Jessie Caverhill Pass, Oakville

Detached for Sale in Oakville

New — Listed 5 days ago
5Beds
5Baths
3,000 - 3,499Sq Ft
Detached
Property Details
MLS Number
W12985726
Property Type
Detached
Status
active
Days on Site
5
Bedrooms
5
Bathrooms
5
Square Feet
3,000 - 3,499 sqft
Neighbourhood
Oakville
Listing Brokerage
RE/MAX ESCARPMENT REALTY INC.
Description

If you've been waiting on the sidelines for the perfect combination of massive living space, untouchable privacy, and incredible value, your wait is officially over. Welcome to 198 Jessie Caverhill Passage-an executive residence on a premium 45-foot lot that checks every single box. This is a rare opportunity, and it is priced to move. Boasting 3,357 square feet of bright, above-ground elegance, this home is built for living large. Step inside to find soaring 9-foot smooth ceilings that carry through both the main and second floors. Stunning, premium hardwood flows flawlessly throughout the entire home. The heart of this property is a true chef's kitchen, fully loaded with upgraded cabinetry, quartz countertops, stainless steel appliances, and a massive center island. That kitchen flows right out into the ultimate game-changer: the backyard. Step outside onto a massive custom deck engineered to host 40 of your closest friends. The best part? You are completely surrounded by towering, mature cedars that deliver total privacy. In this highly sought-after Glenorchy neighborhood, that kind of seclusion is a massive rarity. It's your own private oasis. Head upstairs to find four generously sized bedrooms, including a guest suite featuring a private bath and a charming Juliet balcony. The primary retreat is an absolute showstopper, offering two walk-in closets and a spa-inspired five-piece ensuite complete with a freestanding soaker tub and glass shower. Need more space? Head downstairs to the fully finished, 1,400 square-foot lower level. This complete living suite features a massive rec room, a generous bedroom, a modern full bath, and a functional kitchenette. Whether it's an in-law suite or your premier game day headquarters, the value here is off the charts. With over 4,700 total square feet of finished living space, luxury finishes, and an extremely rare cedar-lined backyard, properties with this kind of immediate upside do not last. Don't sleep on it!

Mortgage Calculator

Estimate your monthly payments for this property

Estimated Payment

$7,961.56/mo

$
$
5%20%50%

5-yr fixed avg.

Principal: $1,439,920Interest: $948,549
Mortgage Amount$1,439,920
Total Interest$948,549
Est. Property Tax$1,275/mo
Total Cost$2,388,469

Rates shown are estimates based on typical Ontario 5-year fixed rates. Canadian mortgages use semi-annual compounding as required by law. CMHC insurance applies to purchases under $1.5M with less than 20% down. Estimated property tax uses an approximate 0.85% rate. Contact us for current rate options and pre-approval.

Ready to get pre-approved?

Know your exact budget before you start house hunting.

Neighbourhood Guide: Oakville

Discover Oakville

Oakville is a vibrant community in the Greater Toronto Area, offering excellent amenities, schools, and transportation options. This area is popular with families and professionals seeking a balanced lifestyle with access to urban conveniences and natural spaces.

Why Live in Oakville

  • Convenient location in Oakville
  • Access to local shops and dining
  • Good public transit connections
  • Community parks and green spaces
  • Well-maintained neighbourhoods

Nearby Schools

Oakville Trafalgar High SchoolPublic High School
Iroquois Ridge High SchoolPublic High School
Holy Trinity Catholic Secondary SchoolCatholic High School
Abbey Park High SchoolPublic High School

Transit & Commuting

  • MiWay bus routes throughout the area
  • GO Transit stations within driving distance
  • Easy highway access to 401/403/QEW
  • Walking distance to local amenities

Parks & Amenities

  • Local parks and recreational facilities
  • Community centres
  • Shopping plazas nearby
  • Restaurants and cafes

Lifestyle & Community

Oakville offers a wonderful quality of life with a mix of residential charm and urban convenience. Residents enjoy easy access to schools, parks, and shopping, making it an ideal location for families and professionals alike.

70
Walk Score
Varies
Price Range

198 Jessie Caverhill Pass, Oakville

Open in Google Maps

Use the map controls to zoom, pan, and switch between map and satellite views. Drag to explore the neighbourhood.

Investor Analysis

Rental income estimator & ROI calculator

Estimated Monthly Rent
$4,200/mo
Range: $3,570 - $4,830
Cap Rate (ROI)
1.7%
Below Average

Monthly Cash Flow Breakdown

Rental Income+$4,200
Maintenance Fees-$0
Property Tax (est.)-$1,275
Insurance (est.)-$375
Net Cash Flow+$2,550

Note: These are estimates only. Actual figures may vary based on market conditions, property condition, and other factors. Consult with a financial advisor for personalized advice.

Joe Battaglia - Top Real Estate Agent in Mississauga, RE/MAX Realty Specialists

Joe's Thoughts

Honest perspective from 30+ years of GTA real estate experience

Competitive Pricing

At $600/sqft, this is priced below the area average. This could represent genuine value, but let's investigate why. In my experience, underpriced homes often have deferred maintenance, unfavourable layouts, or motivated sellers. I'll help you determine which it is.

Just Listed - Act Strategically

This property hit the market within the last week. In Oakville's current market, desirable homes often receive multiple offers within 5-7 days. If you're seriously interested, I recommend booking a showing immediately. However, never let urgency override due diligence - we'll still do proper inspections.

Detached Home Advantages

Detached homes in Oakville are increasingly scarce and valuable. You'll have no shared walls, full control over renovations, and typically stronger appreciation. Consider the lot size and potential for future additions or basement apartment income. Detached homes also offer the most flexibility for growing families.

Larger Home Realities

At 3,000 sqft, this is a substantial home. Budget approximately $400-600/month more for utilities compared to an average-sized home. Maintenance costs scale with size too - roof, HVAC, and cleaning all cost more. That said, space is a luxury that's hard to add later, and larger homes often have better resale in family-oriented neighbourhoods.

Excellent Flexibility

With 5 bedrooms, you have genuine flexibility. Beyond the master and kids' rooms, you can have a dedicated home office, guest room, hobby space, or even rental income potential. In today's work-from-home era, extra bedrooms add significant value. Properties with 5+ bedrooms are relatively rare in Oakville.

Bathroom Count Matters

With 5 bathrooms, morning routines are much smoother. Multiple bathrooms significantly improve daily livability and are a major selling point for resale. Buyers consistently pay more for adequate bathroom counts - this is a strong feature.

Recently Sold Nearby

Recent sales in Oakville to help you understand market values

Similar Properties Nearby

Active listings in Oakville with similar features

Search
Log in